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ETHCHLORVYNOL CIV (0.7 ML)

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ETHCHLORVYNOL CIV (0.7 ML) Basic information

Product Name:
ETHCHLORVYNOL CIV (0.7 ML)
Synonyms:
  • ETHCHLORVYNOL CIV (0.7 ML)
  • (1E)-1-Chloro-3-ethyl-1-penten-4-yn-3-ol
  • beta-chlorvinylethylethynylcarbinol
  • Etchlorvinolo
  • Ethchlorovynol
  • Ethchlorvinol
  • Ethchlorvinyl
  • Ethclorvynol
CAS:
113-18-8
MF:
C7H9ClO
MW:
144.6
Product Categories:
  • Aliphatics
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
113-18-8.mol
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ETHCHLORVYNOL CIV (0.7 ML) Chemical Properties

Melting point:
25°C
Boiling point:
bp760 173-174°; also reported as bp760 181°; bp0.1 28.5-30°
Density 
d425 1.065-1.070; also reported as d420 1.070
refractive index 
nD25 1.4675-1.4800
solubility 
Chloroform (Soluble), Methanol (Slightly)
form 
Oil
pka
12.06±0.29(Predicted)
color 
Colourless
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Safety Information

HS Code 
2905510000
Hazardous Substances Data
113-18-8(Hazardous Substances Data)
Toxicity
LD50 in mice (mg/kg): 290 orally; 240 s.c. (P'an)
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ETHCHLORVYNOL CIV (0.7 ML) Usage And Synthesis

Chemical Properties

Clear Colorless Oil

Originator

Placidyl,Abbott,US,1965

Uses

Controlled substance (depressant). Sedative; hypnotic.

Definition

ChEBI: Propargyl alcohol in which the methylene hydrogens are substituted by ethyl and 2-chlorovinyl groups. A hypnotic and sedative, it is used for treatment of insomnia in some cases where an intolerance or allergy to more commonly used drugs exists.

Manufacturing Process

Acetylene was passed into a stirred solution of 3.05 grams (0.44 mol) of lithium in 300 ml of liquid ammonia until the blue color exhibited by the mixture had disappeared. Ethyl β-chlorovinyl ketone (47.4 grams; 0.40 mol) dissolved in 50 ml dry ether was then added to the resulting solution of lithium acetylide over a period of 20 minutes, during which the color deepened through yellow to reddish-brown. The mixture was stirred under reflux maintained with a Dry Ice condenser for 2 hours. Thereafter, dry ether (200 ml) was added and the ammonia was permitted to evaporate with stirring overnight.
The residue was poured into a slurry of ice and water containing 30 grams (0.50 mol) of acetic acid. After separating the ether layer, the aqueous layer was washed with two 200 milliliter portions of ether. The combined ether extracts were washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated in a stream of pure nitrogen. Three successive distillations of the residue gave 46.3 grams (80.2% yield) of a colorless liquid, boiling point 28.5° to 30°C at 0.1 mm Hg.

brand name

Placidyl (Abbott).

Therapeutic Function

Sedative, Hypnotic

Safety Profile

Poison by ingestion, subcutaneous, intraperitoneal, and intravenous routes. Human systemic effects by ingestion: general anesthesia and thrombocytopenia (reduction in the number of blood platelets). Human effects on newborn by an unspecified route: drug dependency and Apgar score (condtion of newborn). Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of Cl-.

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